114248-23-6

Basic information

• Product Name: 2',2'-DIFLUORO-2'-DEOXYURIDINE
• Synonyms: 2',2'-DIFLUORO-2'-DEOXYURIDINE;2Deoxy-22difluorouridine;2'-Deoxy-2',2'-difluoro-D-uridine;2',2'-Difluorodeoxyuridine;2'-Deoxy-2',2'-difluorouridine ,97%;Uridine,2'-deoxy-2',2'-difluoro-;Gemcitabine impurity C;1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
• CAS NO: 114248-23-6
• Molecular Formula: C₉H₁₀F₂N₂O₅
• Molecular Weight: 264.18
• Product Categories: Bases & Related Reagents;Metabolites & Impurities;Nucleotides;Carbohydrates & Derivatives;Heterocycles
• Mol File: 114248-23-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 147-149°C
• Appearance: /
• Density: 1.69±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Methanol (Slightly), Water (Very Slightly, Heated)
• PKA: 9.39±0.10(Predicted)
• CAS DataBase Reference: 2',2'-DIFLUORO-2'-DEOXYURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',2'-DIFLUORO-2'-DEOXYURIDINE(114248-23-6)
• EPA Substance Registry System: 2',2'-DIFLUORO-2'-DEOXYURIDINE(114248-23-6)

Safety Data

• Hazardous Substances Data: 114248-23-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 114248-23-6 differently. You can refer to the following data:
1. A metabolite product of Gemcitabine
2. A metabolite of Gemcitabine (G305000) in human plasma.

Synthetic route

((2R,3R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluorotetrahydrofuran-2-yl)methyl benzoate (143157-27-1) → Deoxydifluorouridine (114248-23-6)

Conditions	Yield
With ammonia In methanol at 20℃; for 12h; Temperature;	99%
With ammonia In methanol	99%
With ammonia In methanol at 20℃; for 15h;	95.8%

gemcitabine hydrochloride (122111-03-9) → Deoxydifluorouridine (114248-23-6)

Conditions	Yield
With acetic acid; sodium nitrite In water at 20℃; for 48h;	95%
Multi-step reaction with 3 steps 1: pyridine / 15 h / 25 °C 2: acetic acid / water / 14 h / Reflux 3: ammonia / methanol / 15 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: pyridine / 15 h / 25 °C 2: acetic acid / water / 14 h / Reflux 3: ammonia / methanol / 15 h / 20 °C View Scheme

2'-deoxy-2',2'-difluorouridine-3',5'-dibenzoate (1201895-94-4) → Deoxydifluorouridine (114248-23-6)

Conditions	Yield
With ammonia In methanol at 23℃; for 23h;	90%

gemcitabine (95058-81-4) → Deoxydifluorouridine (114248-23-6)

Conditions	Yield
With hydrogenchloride; isopentyl nitrite In 1,4-dioxane; water at 70℃; Inert atmosphere;	68%
Multi-step reaction with 3 steps 1: dmap; pyridine / 3.5 h / 0 - 20 °C / Inert atmosphere 2: acetic acid / Reflux 3: ammonia / methanol / 20 °C View Scheme

2’-deoxy-2’,2’-difluoro-cytidine (103882-84-4) → Deoxydifluorouridine (114248-23-6)

Conditions	Yield
With water; acetic acid for 24h; Heating;

gemcitabine hydrochloride (122111-03-9) → Deoxydifluorouridine (114248-23-6) + α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose (95058-85-8) + 1-(2-deoxy-2,2-difluoro-α-D-erythropentofuranosyl)uracil

Conditions	Yield
With sodium hydroxide at 40℃; for 672h; Mechanism; further reagent, temperature, time;

(2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate (1445381-44-1) → Deoxydifluorouridine (114248-23-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / water / 14 h / Reflux 2: ammonia / methanol / 15 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid / Reflux 2: ammonia / methanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid; water / 12 h / 110 °C 2: ammonia / methanol / 12 h / 20 °C View Scheme

(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester (1334513-02-8) + Deoxydifluorouridine (114248-23-6) → isopropyl ((S)-(((2R,3R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions	Yield
With pyridine; dimethylaluminum chloride In hexane at 0 - 20℃; for 20h; Inert atmosphere; diastereoselective reaction;	87%
Stage #1: Deoxydifluorouridine With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 0 - 20℃; for 1.5h;

tert-butyldimethylsilyl chloride (18162-48-6) + Deoxydifluorouridine (114248-23-6) → C15H24F2N2O5Si

Conditions	Yield
With pyridine; 1H-imidazole at 25 - 50℃; for 12h; Temperature; Inert atmosphere;	85.5%
With pyridine; 1H-imidazole at 20℃;
With 1H-imidazole In pyridine at 20℃;
With 1H-imidazole In N,N-dimethyl-formamide for 8h; Inert atmosphere;

Deoxydifluorouridine (114248-23-6) → 1-((2R,4R,5S)-3,3-difluoro-4-hydroxy-5-(iodomethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Conditions	Yield
With pyridine; 1H-imidazole; iodine; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;	84%

acetic anhydride (108-24-7) + Deoxydifluorouridine (114248-23-6) → 1-((2R,4R,5R)-3,3-difluorotetrahydro-4-acetoxy-5-acetoxymethylfuran-2-yl)pyrimidin-2,4(1H,3H)-dione

Conditions	Yield
With pyridine at 0 - 5℃; for 16h;	81%

4,4'-dimethoxytrityl chloride (40615-36-9) + Deoxydifluorouridine (114248-23-6) → C30H28F2N2O7

Conditions	Yield
With pyridine at 0 - 25℃; Temperature;	77.7%
With pyridine at 0 - 20℃;
With pyridine at 0 - 20℃; for 15h;
With pyridine at 20℃; for 15h;
With pyridine at 20℃; for 15h;

Deoxydifluorouridine (114248-23-6) → 1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-iodouracil (132832-46-3)

Conditions	Yield
With ammonium cerium (IV) nitrate; iodine; acetic acid at 80℃; for 2h; Inert atmosphere;	75%

benzoyl chloride (98-88-4) + Deoxydifluorouridine (114248-23-6) → ((2R,3R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluorotetrahydrofuran-2-yl)methyl benzoate (143157-27-1)

Conditions	Yield
With 4-methyl-morpholine; dmap In tetrahydrofuran at 0 - 5℃; for 8h;	72%

tert-butyldimethylsilyl chloride (18162-48-6) + Deoxydifluorouridine (114248-23-6) → C15H24F2N2O5Si

Conditions	Yield
Stage #1: Deoxydifluorouridine With pyridine; 4,4'-dimethoxytrityl chloride at 0 - 20℃; for 15h; Stage #2: tert-butyldimethylsilyl chloride With 1H-imidazole In dichloromethane at 20℃; for 12h; Stage #3: With acetic acid In water at 20℃; for 20h;	70%

Deoxydifluorouridine (114248-23-6) → C9H9Cl2F2N2O6P (1233921-78-2)

Conditions	Yield
With trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; trichlorophosphate at 20℃; Cooling with ice;	57.3%

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester (1337529-56-2) + Deoxydifluorouridine (114248-23-6) → isopropyl ((S)-(((2R,3R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions	Yield
Stage #1: Deoxydifluorouridine With tert-butylmagnesium chloride In tetrahydrofuran at -10℃; for 1h; Inert atmosphere; Stage #2: (S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester In tetrahydrofuran at 0℃; for 5h; Inert atmosphere;	22%

Deoxydifluorouridine (114248-23-6) → C15H22F2N2O5Si

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine; 4,4'-dimethoxytrityl chloride / 15 h / 0 - 20 °C 1.2: 12 h / 20 °C 1.3: 20 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Reflux View Scheme

Deoxydifluorouridine (114248-23-6) → C16H26F2N2O6Si

Conditions	Yield
Multi-step reaction with 3 steps 1.1: pyridine; 4,4'-dimethoxytrityl chloride / 15 h / 0 - 20 °C 1.2: 12 h / 20 °C 1.3: 20 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Reflux 3.1: sodium hydroxide / 1,4-dioxane; water / 2 h / 20 °C 3.2: 0.5 h / 20 °C / pH 7 View Scheme

Deoxydifluorouridine (114248-23-6) → C32H44F2N2O6Si2

Conditions

Yield

Multi-step reaction with 4 steps 1.1: pyridine; 4,4'-dimethoxytrityl chloride / 15 h / 0 - 20 °C 1.2: 12 h / 20 °C 1.3: 20 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Reflux 3.1: sodium hydroxide / 1,4-dioxane; water / 2 h / 20 °C 3.2: 0.5 h / 20 °C / pH 7 4.1: pyridine; 4,4'-dimethoxytrityl chloride / dichloromethane / 3 h / 0 - 25 °C 4.2: 15 h / 25 °C 4.3: 15 h / 20 °C View Scheme

Deoxydifluorouridine (114248-23-6) → C32H42F2N2O6Si2

Conditions

Yield

Multi-step reaction with 5 steps 1.1: pyridine; 4,4'-dimethoxytrityl chloride / 15 h / 0 - 20 °C 1.2: 12 h / 20 °C 1.3: 20 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Reflux 3.1: sodium hydroxide / 1,4-dioxane; water / 2 h / 20 °C 3.2: 0.5 h / 20 °C / pH 7 4.1: pyridine; 4,4'-dimethoxytrityl chloride / dichloromethane / 3 h / 0 - 25 °C 4.2: 15 h / 25 °C 4.3: 15 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere View Scheme

Deoxydifluorouridine (114248-23-6) → C33H44F2N2O5Si2

Conditions

Yield

Multi-step reaction with 6 steps 1.1: pyridine; 4,4'-dimethoxytrityl chloride / 15 h / 0 - 20 °C 1.2: 12 h / 20 °C 1.3: 20 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Reflux 3.1: sodium hydroxide / 1,4-dioxane; water / 2 h / 20 °C 3.2: 0.5 h / 20 °C / pH 7 4.1: pyridine; 4,4'-dimethoxytrityl chloride / dichloromethane / 3 h / 0 - 25 °C 4.2: 15 h / 25 °C 4.3: 15 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -70 - 0 °C / Inert atmosphere 6.2: 12 h / 0 - 20 °C / Inert atmosphere View Scheme

Deoxydifluorouridine (114248-23-6) → C33H46F2N2O5Si2

Conditions

Yield

Multi-step reaction with 7 steps 1.1: pyridine; 4,4'-dimethoxytrityl chloride / 15 h / 0 - 20 °C 1.2: 12 h / 20 °C 1.3: 20 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Reflux 3.1: sodium hydroxide / 1,4-dioxane; water / 2 h / 20 °C 3.2: 0.5 h / 20 °C / pH 7 4.1: pyridine; 4,4'-dimethoxytrityl chloride / dichloromethane / 3 h / 0 - 25 °C 4.2: 15 h / 25 °C 4.3: 15 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -70 - 0 °C / Inert atmosphere 6.2: 12 h / 0 - 20 °C / Inert atmosphere 7.1: palladium on activated charcoal; hydrogen / methanol / 1 h / 25 °C View Scheme

Deoxydifluorouridine (114248-23-6) → C53H63F2N3O5Si2

Conditions

Yield

Multi-step reaction with 8 steps 1.1: pyridine; 4,4'-dimethoxytrityl chloride / 15 h / 0 - 20 °C 1.2: 12 h / 20 °C 1.3: 20 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Reflux 3.1: sodium hydroxide / 1,4-dioxane; water / 2 h / 20 °C 3.2: 0.5 h / 20 °C / pH 7 4.1: pyridine; 4,4'-dimethoxytrityl chloride / dichloromethane / 3 h / 0 - 25 °C 4.2: 15 h / 25 °C 4.3: 15 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -70 - 0 °C / Inert atmosphere 6.2: 12 h / 0 - 20 °C / Inert atmosphere 7.1: palladium on activated charcoal; hydrogen / methanol / 1 h / 25 °C 8.1: Triphenylsilyl chloride; dmap; triethylamine / acetonitrile / 5 h / 20 °C 8.2: 1 h 8.3: 12 h / 20 °C View Scheme

Deoxydifluorouridine (114248-23-6) → C31H31F2N3O5 (1445381-68-9)

Conditions

Yield

Multi-step reaction with 9 steps 1.1: pyridine; 4,4'-dimethoxytrityl chloride / 15 h / 0 - 20 °C 1.2: 12 h / 20 °C 1.3: 20 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Reflux 3.1: sodium hydroxide / 1,4-dioxane; water / 2 h / 20 °C 3.2: 0.5 h / 20 °C / pH 7 4.1: pyridine; 4,4'-dimethoxytrityl chloride / dichloromethane / 3 h / 0 - 25 °C 4.2: 15 h / 25 °C 4.3: 15 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -70 - 0 °C / Inert atmosphere 6.2: 12 h / 0 - 20 °C / Inert atmosphere 7.1: palladium on activated charcoal; hydrogen / methanol / 1 h / 25 °C 8.1: Triphenylsilyl chloride; dmap; triethylamine / acetonitrile / 5 h / 20 °C 8.2: 1 h 8.3: 12 h / 20 °C 9.1: ammonium fluoride / methanol / 15 h / 25 - 70 °C View Scheme

Deoxydifluorouridine (114248-23-6) → C11H15F2N3O4 (1445381-71-4)

Conditions	Yield
Multi-step reaction with 10 steps 1.1: pyridine; 4,4'-dimethoxytrityl chloride / 15 h / 0 - 20 °C 1.2: 12 h / 20 °C 1.3: 20 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Reflux 3.1: sodium hydroxide / 1,4-dioxane; water / 2 h / 20 °C 3.2: 0.5 h / 20 °C / pH 7 4.1: pyridine; 4,4'-dimethoxytrityl chloride / dichloromethane / 3 h / 0 - 25 °C 4.2: 15 h / 25 °C 4.3: 15 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -70 - 0 °C / Inert atmosphere 6.2: 12 h / 0 - 20 °C / Inert atmosphere 7.1: palladium on activated charcoal; hydrogen / methanol / 1 h / 25 °C 8.1: Triphenylsilyl chloride; dmap; triethylamine / acetonitrile / 5 h / 20 °C 8.2: 1 h 8.3: 12 h / 20 °C 9.1: ammonium fluoride / methanol / 15 h / 25 - 70 °C 10.1: formic acid / water / 15 h / 25 - 35 °C View Scheme
Multi-step reaction with 3 steps 1: pyridine / 15 h / 20 °C 2: 1H-imidazole / dichloromethane / 14 h / 20 °C 3: acetic acid / water / 15 h / 20 °C View Scheme

Deoxydifluorouridine (114248-23-6) → C11H18F2N3O13P3 (1445398-18-4)

Conditions

Yield

Multi-step reaction with 11 steps 1.1: pyridine; 4,4'-dimethoxytrityl chloride / 15 h / 0 - 20 °C 1.2: 12 h / 20 °C 1.3: 20 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Reflux 3.1: sodium hydroxide / 1,4-dioxane; water / 2 h / 20 °C 3.2: 0.5 h / 20 °C / pH 7 4.1: pyridine; 4,4'-dimethoxytrityl chloride / dichloromethane / 3 h / 0 - 25 °C 4.2: 15 h / 25 °C 4.3: 15 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -70 - 0 °C / Inert atmosphere 6.2: 12 h / 0 - 20 °C / Inert atmosphere 7.1: palladium on activated charcoal; hydrogen / methanol / 1 h / 25 °C 8.1: Triphenylsilyl chloride; dmap; triethylamine / acetonitrile / 5 h / 20 °C 8.2: 1 h 8.3: 12 h / 20 °C 9.1: ammonium fluoride / methanol / 15 h / 25 - 70 °C 10.1: formic acid / water / 15 h / 25 - 35 °C 11.1: pyridine; trichlorophosphate; trimethyl phosphite / 1 h / 4 °C 11.2: 2 h / 20 °C 11.3: 2 h / 20 °C View Scheme

Deoxydifluorouridine (114248-23-6) → C36H42F2N2O7Si

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 15 h / 0 - 20 °C 2: 1H-imidazole / dichloromethane / 12 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: pyridine / 15 h / 20 °C 2: 1H-imidazole / dichloromethane / 14 h / 20 °C View Scheme

Deoxydifluorouridine (114248-23-6) + tert-butylchlorodiphenylsilane (58479-61-1) → C25H28F2N2O5Si

Conditions	Yield
With pyridine

Deoxydifluorouridine (114248-23-6) → C45H44F2N2O6Si

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: silver nitrate; 2,4,6-trimethyl-pyridine / dichloromethane / 20 °C View Scheme

Upstream product

• 95058-81-4 gemcitabine 
• 143157-27-1 ((2R,3R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluorotetrahydrofuran-2-yl)methyl benzoate 
• 1445381-44-1 (2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate 
• 122111-03-9 gemcitabine hydrochloride 
• 1201895-94-4 2'-deoxy-2',2'-difluorouridine-3',5'-dibenzoate 
• 103882-84-4 2’-deoxy-2’,2’-difluoro-cytidine 

Downstream Products

• 1445381-68-9 C₃₁H₃₁F₂N₃O₅ 
• 143157-27-1 ((2R,3R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluorotetrahydrofuran-2-yl)methyl benzoate 

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